C7 Further
Chemistry1. Alcohols, carboxylic acids and esters
2. Energy changes in Chemistry3. Reversible reactions and
equilibria4. Analysis5. Green Chemistry
Alcohols, carboxylic acids and
esters
Organic molecules and functional groups
Alcohols, carboxylic acids and esters
•Organic chemistry is the study of carbon-based compounds.•Organic chemistry covers most fuels, plastics and synthetic fibers, as well as drugs and various classes of biomolecules.•Organic molecules are grouped into a number of classes.•The best-known are hydrocarbons, which are made of only carbon and hydrogen.•There are several subclasses of hydrocarbons, the simplest being the "alkanes", which are straight or branch-chained molecules, all joined with single C-C bonds.
•The simplest alkane is methane (CH4), followed by ethane (C2H6), propane (C3H8), butane (C4H10), pentane (C5H12), hexane (C6H14), heptane (C7H16), octane (C8H18), and so on.
Organic molecules and functional groups
Alcohols, carboxylic acids and esters
SOME ORGANIC CHEMISTRY RULES:
•C atoms always make 4 bonds
•H atoms always make just 1 bond
•O atoms always make 2 bonds
So, when you draw a structure, it’s worth checking it to make sure that all the atoms have the right number of bonds.
Organic molecules and functional groups
Alcohols, carboxylic acids and esters
= CH4 or lab or kitchen gas
= C2H6 or used in chemical industry to make
ethene
= C3H8 or camping and BBQ gas
= C4H10 or
Organic molecules and functional groups
Alcohols, carboxylic acids and esters
Alkanes burn in plenty of air to give carbon dioxide and water
Methane CH4(g) + 2O2(g) CO2(g) +
2H20(g)
Ethane 2C2H6(g) + 7O2(g) 4CO2(g) +
6H20(g)
Propane C3H8(g) + 5O2(g) 3CO2(g)
+ 4H20(g)
Butane 2C4H10(g) + 13O2(g) 8CO2(g)
+ 10H20(g)
These are balanced equations with state symbols
Organic molecules and functional groups
Alcohols, carboxylic acids and esters
Calculating reacting masses
Methane CH4(g) + 2O2(g) CO2(g) +
2H20(g)1 x C 1 x C4 x H 4 x H4 x O 4 x 0
Relative atomic masses (from periodic table):C=12, H=1, O=16
These are balanced equations with state symbols
Organic molecules and functional groups
Alcohols, carboxylic acids and esters
Organic molecules and functional groups
Alcohols, carboxylic acids and esters
Calculating reacting masses
Methane CH4(g) + 2O2(g) CO2(g) +
2H20(g)1 x 12 =12 1 x
C=124 x 1 =4 4 x H=44 x 16=64 4 x
0=64Total =80
Total =80
mass of reactants = mass of products
(always! No exception)
Organic molecules and functional groups
Alcohols, carboxylic acids and esters
•The first 4 alkanes are gases and they do not dissolve in water.
•As the hydrocarbon chains get longer the alkanes become oily viscous liquids instead of gases.
•C-C and C-H bonds are unreactive and strong, so the alkanes do not react with aqueous reagents.
•Aqueous reagents = chemicals dissolved in water
Alkanes do not have any functional groups, they are simple hydrocarbon chains.
Alcohols
Alcohols, carboxylic acids and esters
CH
H
H
H
O
METHANOL
CH
H
H
H
O
ETHANOL
C
ALCOHOLS
= CH3OH or
= C2H5OH orH
H
•Chemical feedstock •(to make other chemicals)•Antifreeze•Solvent•Fuel
•Solvent•Fuel•Alcoholic drinks
Alcohols all have a the –OH functional group
Alcohols
Alcohols, carboxylic acids and esters
•The alcohols are liquids and are soluble in water.
•As the hydrocarbon chains the get longer the alcohols become viscous liquids.
•Like in alkanes, the C-C and C-H bonds are unreactive, but the C-O and O-H bonds DO react with other things.
•The properties of alcohols are due to the –OH functional group.
•Alcohols burn in air because of their hydrocarbon chain.
Alcohols
Alcohols, carboxylic acids and esters
•Reaction of alcohols with air (the brandy on your christmas pudding!)
Alcohols burn in air because of the hydrocarbon chain, just like alkanes.
In plenty of air, alcohols burn with a clean blue flame.
C2H5OH(l) + 3O2(s) 3H2O(g) + 2CO2(g)
Alcohols
Alcohols, carboxylic acids and esters
•Reaction of alcohols with metals (eg sodium,a group 1 alkali metal)
If a small piece of sodium is dropped into some ethanol, it reacts steadily to give off bubbles of hydrogen gas and leaves a colourless solution of sodium ethoxide, CH3CH2ONa. Sodium ethoxide is known as an alkoxide.
Although this looks new and complicated, it is exactly the same as the reaction between sodium and water (although gentler!) - something you have probably known about for years.
2C2H5OH(l) + 2Na(s) 2C2H5O-Na+(s) + H2(g)
2H2O + 2Na 2NaOH + H2
Alcohols
Alcohols, carboxylic acids and esters
•Comparing the physical properties of alcohols with water and alkanes
Boiling point(oC)
Melting point (oC)
Density(g/cm3)
Alcohol (eg. ethanol)
78 -114 0.79
Water 100 0 1.0Alkane (eg. ethane)
-89 -183 0.546The hydrocarbon chain in alcohol
and alkane make them less dense than water. They will form a layer on top of water.
Eg. Oil is a hydrocarbon
The –OH group in alcohols makes the boiling point higher, more like water.
This makes alcohol a liquid at room
temperature. Alkanes don’t have the –OH and so
are gases at RT
Carboxylic Acids
Alcohols, carboxylic acids and esters
CH HO
METHANOIC ACID
CH
H
H
H
O
ETHANOIC ACID
C
CARBOXYLIC ACIDS
= HCOOH or
= CH3COOH or
•aka formic acid•The painful chemical in ant stings
•aka acetic acid•Vinegar!
Carboxylic acids all have a the –COOH functional group
O
O
Carboxylic Acids
Alcohols, carboxylic acids and esters
•Most carboxylic acids taste and smell unpleasant (sweaty socks and rancid butter)
•Carboxylic acids react with metals, alkalis and carbonates in the same way as other acids do.
•The properties of carboxylic acids are due to the –COOH functional group.
•Vinegar is a dilute solution of ethanoic acid
Esters
Alcohols, carboxylic acids and esters
•Most carboxylic acids taste and smell unpleasant (sweaty socks and rancid butter)
•Carboxylic acids react with metals, alkalis and carbonates in the same way as other acids do.
•The properties of carboxylic acids are due to the –COOH functional group.
•Vinegar is a dilute solution of ethanoic acid
Esters
Alcohols, carboxylic acids and esters
alcohol + carboxylic acid ester + wateralcohol
Carboxylic acid
ester
water
Esters are characterised by the –COC- group where the acid and
alcohol joined
Esters
Alcohols, carboxylic acids and esters
•Different esters have different, but pleasant smells.
•Can you spot the pattern in naming esters?Alcohol Carboxylic
acidEster Smell of
esterPentanol Ethanoic
acidPentyl ethanoate
Pears
Octanol Ethanoic acid
Octyl ethanoate
Bananas
Pentanol Butanoic acid
Pentyl butanoate
Strawberries
Methanol Butanoic acid
Methyl butanoate
Pineapples
Esters
Alcohols, carboxylic acids and esters
•Esters occur naturally, but can be made in the laboratory by reacting an alcohol with an organic acid. A little sulfuric acid is needed as a catalyst.
•They have distinctive pleasant (usually) smells.
•They are responsible for the smells and flavours of fruits
•They are used in products such as food, perfumes, solvents and plasticisers
•Some esters used in perfumes are natural, while others are synthetic - made artificially.
Esters
Alcohols, carboxylic acids and esters
Esters
Alcohols, carboxylic acids and esters
Making pure esters.
Step 1.The carboxylic acid and alcohol (and a small amount of
sulfuric acid catalyst) are heated under reflux. This
allows them to be heated for a long time so that the reaction can complete without losing
any of the product by evaporation.
Esters
Alcohols, carboxylic acids and esters
Esters
Alcohols, carboxylic acids and esters
Making pure esters.
Step 2.The ester and water mixture is distilled and the
product (ester) collected at it’s boiling point and condensed in
the liebig condenser, then collected in a beaker.
Ethyl ethanoate boils at 77oC
Esters
Alcohols, carboxylic acids and esters
Making pure esters.Step 3.The ester is then purified in a separating funnel by adding sodium
carbonate. This reacts with any remaining acid in the mixture. This
includes any unreacted carboxylic acid as well as the catalyst.
Oily layer (pure ester)Aqueous layer (dissolved salt, made from excess acid)
Esters
Alcohols, carboxylic acids and esters
Fats are esters!!
•Fats are an ester of glycerol and fatty acids that occur naturally.
•Living organisms make fats and oils as an energy store.
Esters
Alcohols, carboxylic acids and esters
Saturated vs unsaturated fatty acidsIn saturated fats, all the carbons
have made bonds with other atoms.
In mono-unsaturated fats, there is ONE double bond between two carbon atoms.
In poly-unsaturated fats, there are many double bonds in the hydrocarbon chain.
•Most animal fats are saturated molecules, all their C-C bonds are single.
•Vegetable oils are mostly unsaturated molecules, they contain C=C double bonds.
Energy changes in Chemistry
Energy Changes in Chemistry
Energy changes in Chemistry
When a reaction takes place, bonds are broken and new chemical bonds are made:
•breaking bonds is an endothermic process, because energy has to be taken in from the surroundings to break the bonds
•making bonds is an exothermic process, because energy is released in the formation of new chemical bonds
•IN EVERY REACTION, SOME BONDS ARE BROKEN AND NEW ONES ARE MADE. The balance of these determines if the overall reaction is endothermic or exothermic
Exothermic reactions
Energy changes in Chemistry
Exothermic Reactions
•An exothermic reaction releases energy.
•The reaction mixture feels hot
•We use exothermic reactions in burning fuels as a source of energy.
Exothermic reactions
Energy changes in Chemistry
This diagram shows the amount of energy stored in the reactants and products of an EXOTHERMIC reaction.Energy out
Endothermic reactions
Energy changes in Chemistry
Endothermic Reactions
•An endothermic reaction takes in energy from its surroundings.
•The reaction mixture feels cold
•More energy is needed to break to bonds of the reactants than is released in forming products.
Endothermic reactions
Energy changes in Chemistry
This diagram shows the amount of energy stored in the reactants and products of an ENDOTHERMIC reaction.
Energy in
Activation Energy
Energy changes in Chemistry
Activation Energy
...is the energy needed to break bonds to start a reaction. Like getting a boulder rolling over the edge of a cliff!
...we provide activation energy or lower it by:•Heating the reactants•Using a catalyst•Making the reactants more concentratedAll of these will increase the rate of reaction
Activation Energy
Energy changes in Chemistry
Bond energies
Energy changes in Chemistry
The energy needed to break apart a bond between two particular atoms is known as bond energy. Bond energies are measured in kJ and we can use them to work out energy change in reactions.Some of the most common bond energies are displayed below:
Energy Calculations – Worked Example 1
Energy changes in Chemistry
Burning hydrogen in oxygen.
Hydrogen + oxygen water
2H2(g) + O2(g) 2H2O(g)
First we look up all the bond energies on either side of the reaction. You don’t need to learn these!:H-H is 436kJ O=O is 496kJ O-H is 436kJ
H H
H HO O H H
OH H
O
Energy Calculations – Worked Example 1
Energy changes in Chemistry
2H2(g) + O2(g) 2H2O(g)
Bonds broken:2 x H-H and 1 x O=O
= (2 x 436) + 496= 872 + 496= 1368kJ
H H
H HO O
Bonds made:4 x O-H
= 4 x 463= 1852kJ
H HO
H HO
H-H is 436kJO=O is 496kJO-H is 463kJ
Energy change = start – finish= 1368 – 1852= -484kJ
MORE ENERGY IS USED TO MAKE BONDS THAN BREAK THEM. IT IS AN EXOTHERMIC REACTION.
484kJ of heat is
given out
Energy Calculations – Worked Example 2
Energy changes in Chemistry
Hydrogen and halogens react to form hydrogen halides.
Hydrogen + chlorine hydrogen
chlorideH2(g) + Cl2(g) 2HCl(g)First we look up all the bond energies on either side of
the reaction. You don’t need to learn these!:H-H is 436kJ Cl-Cl is 243kJ H-Cl is 432kJ
H H Cl Cl H Cl
H Cl
Energy Calculations – Worked Example 2
Energy changes in Chemistry
H2(g) + Cl2(g) 2HCl(g)
Bonds broken:1 x H-H and 1 x Cl-Cl
= 436 + 243= 679kJ
H H Cl Cl
Bonds made:2 x H-Cl
= 2 x 432= 864kJ
H-H is 436kJCl-Cl is 243kJH-Cl is 432kJ
Energy change = start – finish
= 679 – 864= -185kJ
185kJ of heat is
given out
H ClH Cl
MORE ENERGY IS USED TO
MAKE BONDS THAN BREAK
THEM. IT IS AN EXOTHERMIC
REACTION
Endothermic reactions
Energy changes in Chemistry
Which of the worked examples gives out the most heat energy?1. Hydrogen and oxygen2. Hydrogen and chlorine
HYDROGEN AND OXYGEN!
Which is what went wrong with the Zeppelin airship in 1937. It was filled with hydrogen (lighter than air), but a stray spark provided the activation energy to start the reaction between the hydrogen and oxygen in air. It exploded spectacularly!
The Hindenburg Disaster
Reversible reactions
and equilibria
Reversible reactions
Reversible reactions and equilibria
In KS3 you looked at the difference between physical and chemical reactions. You will remember that there are signs that a CHEMICAL reaction is happening:•Colour change•Temperature change•Bubbles of gas formed•Cannot be easily reversed
This was an oversimplification! Some reactions are quite easily reversed.... REVERSIBLE REACTIONS
N2(g) + 3H2(g) 2NH3(g)
Note the different type of arrow used for
reversible reactions
N2(g) + 3H2(g) 2NH3(g)
In a closed system, where none of the reactants or products can escape, the reaction will reach DYNAMIC EQUILIBRIUM. This means it’s going forward and backwards at the same rate.
Dynamic Equilibrium
Reversible reactions and equilibria
Pure reactants –
no products
formed yet
Pure products –
no reactants
leftProducts and
reactants cycling at same rate. Reaction will
appear to have stopped
Strong acids and weak acids
Reversible reactions and equilibria
Diluting a strong acid in water does not change its pH (otherwise dilution would turn an acid into an alkali!)
Dynamic equilibrium explains why some acids are weak and others are strong
Some strong acids are:•Hydrochloric acid - HCl•Nitric acid - HNO3•Sulfuric acid - H2SO4
Carboxylic acids are weak acids
Strong acids and weak acids
Reversible reactions and equilibria
How strong is an acid?When an acid dissolves in water, it forms H+ ions. This is a hydrogen atom which has lost an electron (a proton).
The strength of an acid depends on the how much it ionises in water.
HCl(g) H+(aq) + Cl-(aq)
A strA strong acid or alkali is one which is completely (100%) ionised in water. Equilibrium is to the right.
Strong acids and weak acids
Reversible reactions and equilibria
PRODUCTSREACTANTSHCl H++ Cl-
A strong acid or alkali is one which is completely ionised in water. Equilibrium is to the right. eg hydrochloric acid
PRODUCTSREACTANTSHCOOH H++ HCOO-
A weak acid or alkali is one which is only partly ionised in water. Equilibrium is NOT far over to the right. eg. methanoic acid
Strong acids and weak acids
Reversible reactions and equilibria
pH is a measure of how ionised an acid is. It measures the concentration of
hydrogen ions
Analysis
Qualitative vs. quantitative
Analysis
Qualitative analysis
Describes some quality of a substance eg. It is blue, it smells of rotten eggs
Quantitative analysis
Tells us how much of a substance is present (its quantity) eg. 16 g/mlAs a general rule. If you are given data with
numbers in it, then its probably quantitative data, like continuous data in maths. If it is discrete data, then it is likely to be qualitative.
Sampling methods
Analysis
•When collecting data samples should represent the bulk of the material being tested
•This is done by taking many samples at random
•Multiple random sampling allows us to be more confident in our conclusion
Standard Procedures
Analysis
•We use standard procedures for handling samples
•This ensures that the results are reliable, since there’s less chance of human error
•Standard procedures are similar to following a recipe to get the same results each timeSamples should be:
1. Collected in a sterile container2. Sealed3. Labelled4. Stored in a safe place
Standard Procedures
Analysis
•Sports men and women have to provide urine samples to check they have not been taking drugs this is done in front of a testing officer to ensure it is not tampered with and labelled with a unique code so the lab does not know the identity of the athlete
•2 samples of urine are taken from sports people one is analysed immediately and one is frozen in case there is a query at a later date
Standard Procedures in the news
Analysis
Chromatography
Analysis
Chromatography is used to find out what is unknown mixtures are made up of.
This is done by comparing the unknown mixture with known reference samples
Colourless samples can be separated and then revealed by locating agents
Chromatography can be qualitative or quantitative
Chromatography
Analysis
•Stationary (not moving) phase = paper•Mobile (moving) phase = solvent
•Substances are separated as they move between the mobile and stationary phases
•Some substances stay dissolved in the solvent for longer
•Others are more attracted to the stationary phase and stay there
Comparing the spots gives us
qualitative data
Chromatography
Analysis
Chromatography Solvents
Analysis
Chromatography solvents (mobile phases)
Aqueous Non-aqueous
Water based
Made from organic liquids, like alkanes or
alcoholsThere is a dynamic equilibrium between the mobile and stationary phases at the point where the chemical comes out of the solvent.
Paper Chromatography
Analysis
The 5 steps in paper chromatography
If the substance analysed is a solid,
dissolve it in a suitable solvent
Put a spot of the solution close to the
bottom of the chromatography
paper, allow to dry
Put the bottom edge of the paper into the solvent, not touching
the sample The solvent rises up the paper, dissolves
the spot and carries it up the paper
The different chemicals in the mixture travel different distances according to how
soluble they are in the solvent
1
23
4
5
Thin Layer Chromatography
Analysis
Thin layer chromatography•Thin layer chromatography is a more sophisticated technique than paper chromatography
•Can work with smaller samples
•Gives better separation of samples
•Done on a stationary phase of glass, plastic, or aluminum foil, which is coated with a thin layer of adsorbent material, usually silica gel, aluminium oxide, or cellulose
Quantitative Chromatography - calculating Rf value
Analysis
Solvent Front
Sample start point
Solvent start point
Rf = distance moved by sample distance moved by solvent
Worked examples:
Rf = 5.5 = 0.92 6.0
Rf = 3.0 = 0.50 6.0
Quantitative Chromatography - calculating Rf value
Analysis
Chromatography locating agents
Analysis
Using ultra violet light to as a locating agent, to reveal a sample that would otherwise be invisible
Gas Chromatography
Analysis
Gas chromatography•Used to separate complex organic mixtures•Mobile phase is an unreactive gas (helium, nitrogen)•Stationary phase is a liquid layer on the inside surface of a column•Sample is injected into machine•Sample is vaporised and then carried through the column•Samples form dynamic equilibrium between mobile and stationary phases•Computer calculates exact quantities of each part of the mixture
Organic compounds have known retention times, they can be identified by looking up the values of the unknowns
Interpreting Gas Chromatographs
Analysis
•The position of the peak identifies the compound•The area of the peak is used to calculate the quantity of material in the sample
•eg. There is a lot more linoleic acid than arachidic acid. There is very little linolenic acid in this sample.
Main Stages of Quantitative Analysis
Analysis
a.Measuring out accurately a specific mass or volume of the sample
b.Working with repeated samplesc.Dissolving the samples in known volumesd.Measuring and getting a quantitative
resulte.Calculating a value from the
measurements (eg the mean/min/max)f. Estimating the degree of certainty in the
resultsThis should be familiar, it is exactly what you did in your
coursework
Standard Solutions
Analysis
• Solutions are a mixture of a chemical in a solvent (usually water)
• Concentration of a chemical in solution is given in g/dm3 (grams of chemical in every litre of the solution)
• The concentrations of standard solutions are known accurately so they can be used to compare the concentration of other solutions
Standard Solutions
Analysis
Preparing a standard solution
Calculating Concentration and Mass
Analysis
Calculate the concentration of a solution using this formula:
Concentration (g/dm3) = mass (g)
volume (dm3)
SWEET TEA!!Worked example:Calculate the concentration of the solution when 12.6g of sucrose is dissolved in 350cm3 water
First convert cm3 to dm3 by dividing by 1000... 350/1000 = 0.35dm3
Then calculate the concentration... 12.6g/0.35dm3 = 36g/dm3
Calculating Concentration and Mass
Analysis
Calculate the mass of solute by transposing the formula:mass (g) = concentration (g/dm3) x volume (dm3) Worked example:Calculate the mass of solute in solution when the concentration is 26 g/dm3 and the volume is 0.2dm3
All volumes are given in dm3 so no need to convert any
Mass = 26g/dm3 x 0.2dm3
= 5.2 g
Titration of acid with alkali
Analysis
•Acid/alkali titration is a common kind of quantitative analysis
•It is used to work out the concentration of an acid, by titrating it with a known concentration of alkali
•Reacting masses can be used to calculate the concentration of the acid solution
Titration
Titration of acid with alkali
Analysis
Titration of acid with alkali
Analysis
Titration Calculations
Analysis
Calculate the concentration of hydrochloric acid when...
•Concentration of sodium hydroxide (NaOH) = 25 g/dm3
•Volume of sodium hydroxide = 57 cm3
The experiment was done 3 times and the volume of acid used recorded, The results were:1. 10.0cm3
2. 9.9cm3
3. 10.1cm3
Mean = 10.0 + 9.9 + 10.1 = 10.0 cm3
3
Worked exam
ple
Titration Calculations
Analysis
Calculate the concentration of hydrochloric acid when...
•Concentration of sodium hydroxide (NaOH) = 10 g/dm3
•Volume of sodium hydroxide = 50 cm3
•Mean volume of HCl used = 10.0 cm3
(=0.01dm3)HCl + NaOH NaCl + H2Oconcentratio
n of acid (g/dm3)
= Volume (dm3) x concentration of NaOH (g/dm3)Volume of HCl (dm3)
= 50 dm3 x 10g/dm3
0.01 dm3
= 500 g/dm3
Worked exam
ple
How reliable are the results?
Analysis
•The accuracy of an experiments results affects how valid the results are•Inaccurate results are often caused by human error•A wide range of values leads to lack of certainty and is not precise
Calculating degree of uncertainty
Analysis
•Calculate the mean of your results•Find the range of your results
Results of 5 titrations54.7 g/dm3
49.3 g/dm3
53.1 g/dm3
52.2 g/dm3
54.3 g/dm3
Mean = 52.7 g/dm3
Range = 49.3 to 54.7 g/dm3
Degree of uncertainty = range = 5.4 g/dm3
Percentage error = (degree of uncertainty / mean)*100
= (5.4/52.7)*100= 10.2%
Certainty = 100 – 10.2 = 89.8%
GreenChemistry
Production of chemicals
Green Chemistry
Making useful chemicals for industry involves several stages:
oPreparation of feedstocks (large quantities of reactants)oSynthesisoSeparation of productsoHandling of by-products and wasteoMonitoring purity
Green Chemistry is about making these processes as sustainable as possible
•.
No wasted atoms
Using renewable feedstocks
Energy in and out
Health and safety risks
Reducing and controlling waste
Environmental impact
Social and economic benefits
Bulk and fine chemicals
Green Chemistry
BULK CHEMICALS are made on a large scale - to fairly low quality•Ammonia•Sulfuric acid•Sodium hydroxide•Phosphoric acidFINE CHEMICALS are made on a small scale - to a very high quality•Drugs•Food additives•Fragrances
Mostly chemicals for agriculture or
as chemical feedstocks
Mostly for human consumption, quality strictly
monitored
Bulk and fine chemicals
Green Chemistry
There is a lot of green chemical industry research into catalysts because:
•They reduce the activation energy needed by a reaction
•They make the reaction faster and more efficient
•They remain unchanged and can be used repeatedly, making the process more sustainable
All new chemicals are the result of a lot of
research and development.
Government has strict controls on chemical
processes as well as on storage and transport
of chemicals.
This is to protect people and the environment
Making ethanol
Green Chemistry
There are 3 ways of making ethanol:•Synthesis•Fermentation•Biotechnology
CH
H
H
H
OC
H
H
C2H5OH
Making ethanol
Green Chemistry
Why do we need to make large quantities of ethanol?:•Fuel•Feedstock for chemical industry•Alcoholic beverages•Antiseptic•Solvent
Making ethanol – Synthesis method
Green Chemistry
•All hydrocarbons come originally from crude oil•The oil undergoes fractional distillation, to split its hydrocarbons up according to chain length•This is not sustainable
Making ethanol – Synthesis method
Green Chemistry
Ethanol can be made from another organic compound, ethene.•Crude oil is fractionated,
and then the longer chain alkanes are cracked into shorter ones by heat and a catalyst
•Ethene is one of the products of cracking
•Cracked ethene is then used as a feedstock for manufacture of ethanol
•Ethene reacted with steam at high temperature and pressure, with a catalyst, to make ethanol
C2H4(g) + H2O(g) C2H5OH(g)
Ethene is an unsaturated
version of ethane, the C=C bond is a
double bond
•Unreacted reactants are recycled and fed through the system again
ethene + water ethanol
Making ethanol – Fermentation method
Green Chemistry
Ethanol can be made by fermenting sugar.
C6H12O6 (aq) 2C2H5OH(aq) + 2CO2 (aq) •Ethanol for alcoholic beverages industry is made this way•Yeast provides the enzymes that make the reaction happen•Carried out at room temperature so the yeast isn’t denatured•Carbon dioxide is allowed to escape from the reaction vessel, but air is kept out, to keep the product clean
Making ethanol – Fermentation method
Green Chemistry
Ethanol made by fermentation has a limited concentration•The concentration of the alcohol is limited by:
• the temperature – if it’s too high the enzyme is denatured
• the amount of sugar in the mixture – once it’s gone, it’s gone
• the pH of the reaction mixture – if it changes too much the enzyme is denatured
Making ethanol – Fermentation method
Green Chemistry
Ethanol can be made stronger by distillation.
Distillation on a small scale
•Ethanol boils at 78oC
•Heat the ethanol and water mixture to 78oC
•Collect and condense the gases at this temperature
•This is pure ethanol
•The water is still in the first flask, at that temperature it won’t have boiled
Making ethanol – Biotechnology method
Green Chemistry
Ethanol can be made by GM bacteria•The bacteria, e-coli can be genetically modified to
help produce ethanol from waste biomass
•Waste biomass includes corn stalks and remains of fruit that has been used to produce juice.
•The steps in this process are:: 1: The waste biomass is cut into small pieces. 2: The genetically modified e-coli converts the waste biomass into sugars. 3: The sugars produced are fermented. 4: The ethanol produced is distilled.
Making ethanol – assessing sustainability
Green Chemistry
There are drawbacks to every method
• Fermentation can only produce small yields of ethanol.
• Production from ethene is very energy intensive and the greenhouse gas, carbon dioxide is produced as a waste product.
• Using waste biomass is a green option, but the waste biomass is often used for other things, such as feeding animals. This means other biomass now needs to be used to feed these animals.